NDLI: Synthesis of rigid tryptophan mimetics by the diastereoselective Pictet-Spengler reaction of ß³-homo-tryptophan derivatives with chiral -amino aldehydes.

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Synthesis of rigid tryptophan mimetics by the diastereoselective Pictet-Spengler reaction of ß³-homo-tryptophan derivatives with chiral -amino aldehydes.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Slupska, Marta Pulka-Ziach, Karolina Deluga, Edyta Sosnowski, Piotr Wilenska, Beata Kozminski, Wiktor Misicka, Aleksandra
Description	Country affiliation: Poland Author Affiliation: Slupska M ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.); Pulka-Ziach K ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.); Deluga E ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.); Sosnowski P ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.); Wilenska B ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.); Kozminski W ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.); Misicka A ( Faculty of Chemistry, University of Warsaw, Warsaw, Poland.)
Abstract	The Pictet-Spengler (PS) cyclizations of ß(3)-hTrp derivatives as arylethylamine substrates were performed with L- -amino and D- -amino aldehydes as carbonyl components. During the PS reaction, a new stereogenic center was created, and the mixture of cis/trans 1,3-disubstituted 1,2,3,4-tetrahydro-ß-carbolines was obtained. The ratio of cis/trans diastereomers depends on the stereogenic centre of used amino aldehyde and the size of substituents. It was confirmed by 1H and 2D NMR (ROESY) spectra. The conformations of cyclic products were studied by 2D NMR ROESY spectra. Products of the PS condensation after removal of protecting group(s) can be incorporated into a peptide chain as tryptophan mimetics with the possibility of the ß-turn induction.
File Format	HTM / HTML
ISSN	10752617
Issue Number	12
Volume Number	21
e-ISSN	10991387
Journal	Journal of Peptide Science
Language	English
Publisher	Wiley
Publisher Date	2015-12-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Biochemistry Aldehydes Chemistry Peptides Chemical Synthesis Tryptophan Biomimetic Materials Cyclization Magnetic Resonance Spectroscopy Molecular Conformation Molecular Structure Stereoisomerism Journal Article Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Structural Biology Medicine Drug Discovery Biochemistry Molecular Biology Pharmacology Molecular Medicine

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4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
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